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With methanol; sodium tetrahydroborate; at 23℃; for 4h;
Step 1 : To a stirred solution of methyl 2-fluoro-4-nitrobenzoate (10.0 g, 49.7 mmol, 1 eq.) in methanol (100 mL) was added sodium borohydride (9.40 g, 248.7 mmol, 5 eq.) at RT and stirred for 4h. The methanol was evaporated and the residue was diluted with ethyl acetate (50 mL x 2) washed with water (50 mL) and brine (50 mL). The ethyl acetate layer was dried over Na2S04, evaporated under vacuum to get (2-fluoro-4-nitrophenyl)methanol (8 g, 94%, off-white solid; TLC system: EtOAc/PE (3:7), Rf: 0.30).
94%
With methanol; sodium tetrahydroborate; at 23℃; for 4h;
Step 1 : To a stirred solution of methyl 2-fluoro-4-nitrobenzoate (10.0 g, 49.7 mmol, 1 eq.) in methanol (100 mL) was added sodium borohydride (9.40 g, 248.7 mmol, 5 eq.) at RT and stirred for 4h. The methanol was evaporated and the residue was diluted with ethyl acetate (50 mL x 2) washed with water (50 mL) and brine (50 mL). The ethyl acetate layer was dried over Na2SO4, evaporated under vacuum to get (2-fluoro-4-nitrophenyl)methanol (8 g, 94%, off-white solid; TLC system: EtOAc/PE (3:7), Rf: 0.30).
3.6 g
With methanol; sodium tetrahydroborate; at 20℃; for 4.5h;
Into a 500-mL round-bottom flask, was placed methyl 2-fluoro-4-nitrobenzoate (10 g, 50.2 mmol) in methanol (100 mL). This was followed by the addition of NaBH4 (9.5 g, 251 mmol) in portions over 30 mm. The resulting solution was stirred for 4 h at RT. The resulting solution was diluted with 400 mL of ethyl acetate. The resulting mixture was washed with 200 mL ofwater and 200 mL of brine. The organic layer was dried over anhydrous sodium sulfate andthen concentrated. This resulted in 3.6 g of the title compound as an off white solid. MS-ESI:172 (M+1).
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